Capture the Flag is the ultimate test of hacker skill, and DEF CON is the oldest and most prestigious CTF venue. After five years running DEF CON CTF with Legitimate Business Syndicate, our journey running this series of games has come to a close, but what remain are the lessons we learned along the way.

This presentation will cover topics about all aspects of CTF organization: the history of CTF, building a cross-functional organizing team that sticks together year after year, developing a game infrastructure that handles the onslaught of attacks from players, and the stories behind some of the most difficult CTF challenges ever built.